Benzoanellated Centropolyquinanes, 15. Benzoanellated Fenestranes with [5.5.5], [5.5.5.6], and [5.5.5.5] Frameworks: The Route from 1,3-Indandione to Fenestrindan

Kuck D (1994)
Chemische Berichte 127(2): 409-425.

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Abstract / Bemerkung
The synthesis and spectroscopic characterization of several benzoanellated [5.5.5]-, [5.5.5.6]-, and [5.5.5.5]fenestranes, including the parent difuso-centrotriindan 7, the parent tetrafuso-centrotetraindan 8 (fenestrindan) as well as the tribenzo[5.5.5.6]- and tribenzo[5.5.5.5]fenestranes 27 and 35, are described and discussed in full experimental detail. The highly efficient twofold cyclodehydration of 2,2-dibenzyl-1,3-indandiol 15 and the related spiro-condensed 1,3-indandiols 23 and 29 is the keystep of the synthetic strategy. The new synthetic variant involving the one-pot cyclodehydration/deketalization of the dispiro-ketal diol 29 is particularly convenient. In the case of 7, an alternative Lewis acid-catalyzed double cyclization has been developed. Stereochemical aspects of the 1,3-indandiols and the key tribenzo[5.5.5.6]fenestranes 24 and 25 are discussed in detail.
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Zeitschriftentitel
Chemische Berichte
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127
Zeitschriftennummer
2
Seite
409-425
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Kuck D. Benzoanellated Centropolyquinanes, 15. Benzoanellated Fenestranes with [5.5.5], [5.5.5.6], and [5.5.5.5] Frameworks: The Route from 1,3-Indandione to Fenestrindan. Chemische Berichte. 1994;127(2):409-425.
Kuck, D. (1994). Benzoanellated Centropolyquinanes, 15. Benzoanellated Fenestranes with [5.5.5], [5.5.5.6], and [5.5.5.5] Frameworks: The Route from 1,3-Indandione to Fenestrindan. Chemische Berichte, 127(2), 409-425. doi:10.1002/cber.19941270218
Kuck, D. (1994). Benzoanellated Centropolyquinanes, 15. Benzoanellated Fenestranes with [5.5.5], [5.5.5.6], and [5.5.5.5] Frameworks: The Route from 1,3-Indandione to Fenestrindan. Chemische Berichte 127, 409-425.
Kuck, D., 1994. Benzoanellated Centropolyquinanes, 15. Benzoanellated Fenestranes with [5.5.5], [5.5.5.6], and [5.5.5.5] Frameworks: The Route from 1,3-Indandione to Fenestrindan. Chemische Berichte, 127(2), p 409-425.
D. Kuck, “Benzoanellated Centropolyquinanes, 15. Benzoanellated Fenestranes with [5.5.5], [5.5.5.6], and [5.5.5.5] Frameworks: The Route from 1,3-Indandione to Fenestrindan”, Chemische Berichte, vol. 127, 1994, pp. 409-425.
Kuck, D.: Benzoanellated Centropolyquinanes, 15. Benzoanellated Fenestranes with [5.5.5], [5.5.5.6], and [5.5.5.5] Frameworks: The Route from 1,3-Indandione to Fenestrindan. Chemische Berichte. 127, 409-425 (1994).
Kuck, Dietmar. “Benzoanellated Centropolyquinanes, 15. Benzoanellated Fenestranes with [5.5.5], [5.5.5.6], and [5.5.5.5] Frameworks: The Route from 1,3-Indandione to Fenestrindan”. Chemische Berichte 127.2 (1994): 409-425.
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